Large areas of ground are permanently supported on coal pillars, both in extensive old workings and current drivages in active mining operations. Continued growth of civil infrastructure is resulting in more surface development above old bord and pillar mines and an increased need for mine development beneath existing surface structures and features. The result is a greater likelihood of conflict between miners, developers and regulatory bodies. However, over the last 40 years there has also been significant improvement in the general level of understanding of pillar behaviour and stability, both in Australia and overseas. This paper examines some of the issues to be considered when undermining surface structures or undertaking surface development above old workings. The Factor of Safety (FoS) methodology widely employed for the assessment of pillar stability is reviewed, including the key geometrical, geological and statistical concepts associated with the probability of pillar failure; local and international experiences are examined and significant parameters isolated. Common concerns are addressed in the context of actual practical experience, utilising a risk management approach. Recent advances in methods for the assessment of pillar stability are put forward, along with criteria for arriving at rational design outcomes.